Atropo-diastereoselective coupling of aryllithiums and arynes - variations around the chiral auxiliary

被引：14

作者：

Augros, David ^{[1
]}

Yalcouye, Boubacar ^{[1
,2
]}

Berthelot-Brehier, Anais ^{[1
,2
]}

Chesse, Matthieu ^{[1
,2
]}

Choppin, Sabine ^{[2
]}

Panossian, Armen ^{[1
]}

Leroux, Frederic R. ^{[1
]}

机构：

[1] Univ Strasbourg ECPM, CNRS, UMR 7509, COHA, 25 Rue Becquerel, F-67087 Strasbourg, France

[2] Univ Strasbourg ECPM, CNRS, UMR 7509, SynCat, 25 Rue Becquerel, F-67087 Strasbourg, France

来源：

TETRAHEDRON | 2016年 / 72卷 / 34期

关键词：

Biaryl; Aryne C-C coupling; Atropo-diastereoselective; Organolithium; Sulfoxide; Oxazoline; Diether; BIARYL NATURAL-PRODUCTS; ASYMMETRIC-SYNTHESIS; 1,2,3-TRISUBSTITUTED BENZENES; ATROPOSELECTIVE SYNTHESIS; ORGANOLITHIUM COMPOUNDS; KINETIC RESOLUTION; TOLYL SULFOXIDES; PHENYL LITHIUM; BOND FORMATION; OXAZOLINES;

D O I：

10.1016/j.tet.2016.01.047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The atropo-selective coupling of in situ generated arynes and aryllithiums bearing various chiral auxiliaries ortho to lithium (tert-butylsulfoxide, para-tolylsulfoxide, tartrate-derived chiral diethers and oxazolines) is described. Chiral oxazolines showed the best results in terms of yields of coupling products. Different reaction parameters like the nature of the aryne precursor, the oxazoline, the alkyllithium base or the solvent revealed to be crucial for obtaining good yields and for diastereoselection. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：5208 / 5220

页数：13

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